Selectivity controlled by ligand tuning in the palladium-catalysed cyclocarbonylation: Synthesis of new γ and δ lactones from a natural sesquiterpene - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Molecular Catalysis A: Chemical Année : 2015

Selectivity controlled by ligand tuning in the palladium-catalysed cyclocarbonylation: Synthesis of new γ and δ lactones from a natural sesquiterpene

Résumé

The cyclocarbonylation of homoallylic alcohols, derived from α-atlantone, catalysed by [Pd(Cl2)L2]/SnCl2] system, afforded new γ and δ lactones as the main products with high selectivities. The regiochemical control depends on the nature of phosphines involved. Catalysts based on monophosphines with large cone angles such as tricyclohexyl phosphine produce the six-membered ring lactones with selectivities up to 80%, while diphosphines with wide bite angle such as xantphos are found to favor the five-membered ring lactones with up to 99% selectivity. Monocrystals of the γ and δ lactones suitable for X-ray diffraction analysis have been obtained and the stereochemistry of the lactones 5a,a′ and 6 have been elucidated. This study is the first example of an attractive catalytic transformation of one single natural sesquiterpene easily available from bio-renewable resources to obtain either γ- or δ-lactones.
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Dates et versions

hal-01913098 , version 1 (06-11-2018)

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Jamal El Karroumi, Abderrahim El Haib, Eric Manoury, Ahmed Benharref, Jean-Claude Daran, et al.. Selectivity controlled by ligand tuning in the palladium-catalysed cyclocarbonylation: Synthesis of new γ and δ lactones from a natural sesquiterpene. Journal of Molecular Catalysis A: Chemical, 2015, 401, pp.18-26. ⟨10.1016/j.molcata.2015.02.010⟩. ⟨hal-01913098⟩
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